Norman Rockwell liked to quote artist John Singer Sargent on the subject of portraiture. Sargent defined a portrait as “a painting of someone with something wrong with his mouth.” In fact, Rockwell often viewed his art in terms of other artists’ themes and methods, often visiting museums or studying his reference collections of prints and books for inspiration. In his lifetime, Rockwell drew and painted well over two hundred portraits.

Rockwell painted portraits of friends, fellow illustrators, business acquaintances and family members. Their uses varied from book jacket covers to boardroom wall hangings to family heirlooms. In addition, he was commissioned to do portraits of noted celebrities and politicians for magazine covers, including TV Guide and The Saturday Evening Post. The request for a Rockwell portrait became so common that by the 1970s Rockwell was answering many of them with two form letters. The first was a polite decline, citing his work schedule as too heavy to take on new projects; the second was customized for those commissions he felt compelled to accept or was willing to entertain. “It is not in the mainstream of my work, but under certain requirements and circumstances I enjoy painting them.”